Hotels in Chestertown

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Top Rated Chestertown Hotels

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Hotels in Chestertown

    Driftwood Inn

Pet Friendly Chestertown Hotels

    Comfort Inn & Suites Chestertown
    Driftwood Inn
    Great Oak Manor

Where should you stay in Chestertown?

What are some of the best hotels to stay with the kids in Chestertown?

Book one of these hotels for you and the kids in Chestertown. Driftwood Inn is a property offering free parking, free WiFi, and in-room refrigerators. You and your family can also consider Red Roof Inn & Suites Chestertown, a hotel offering free parking, laundry facilities, and free WiFi.

What are some favorite hotels in downtown Chestertown?

These are some of the most popular hotels in downtown Chestertown:

Though not in the heart of Chestertown, you may want to visit famous sights in the larger area like Chesapeake Bay Bridge and White Marsh Mall.

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